


Blessings in Disguise

by Mrs_SimonTam_PHD



Category: Supernatural
Genre: Bad Binding Practices, God is a Fairy Godfather, M/M, Occasions of Deadnaming, Pegging, Season 4 AU, Severe Dysphoria, Severe Transphobia, Sex Toys, bottom!Chuck, self deprecation, self hate, this has a happy ending, top!dean, trans!Dean
Language: English
Status: Completed
Published: 2019-10-22
Updated: 2019-10-22
Packaged: 2020-12-28 02:15:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,550
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21129119
Author URL: https://archiveofourown.org/users/Mrs_SimonTam_PHD/pseuds/Mrs_SimonTam_PHD
Summary: When Castiel raised Dean from Hell, he also undid the transmasc surgeries that Dean had gotten and reformed him into a girl. Dean then reembarks on a journey he thought he left behind over a decade ago and finds a way to love himself again, thanks to an unlikely source.





	Blessings in Disguise

**Author's Note:**

  * For [ScooBiNatural (coldishcase)](https://archiveofourown.org/users/coldishcase/gifts), [Lucifers_perfect_angel](https://archiveofourown.org/users/Lucifers_perfect_angel/gifts).

> **THIS FIC CONTAINS TRANSPHOBIA AND CONTAINS SEVERE DYSPHORIA. IF YOU ARE SENSITIVE TO THIS KIND OF THING, AND YOU NEED TO X OUT OF THE FIC FOR YOUR MENTAL HEALTH, PLEASE DO SO. DO NOT READ AT THE RISK OF TRIGGERING YOURSELF. **
> 
> ALSO, DO NOT BIND WITH ACE BANDAGES. THIS IS DANGEROUS TO YOUR HEALTH. DEAN DOES IT, THAT DOESN'T MEAN YOU SHOULD. 
> 
> *ahem* 
> 
> This fic was asked for by @scoobinatural for @lucifers-perfect-angel!! They had asked for a trans!Dean/Chuck fic and actually, I learned a lot about this process writing this and cried a lot of fucking tears. 
> 
> This fic was beta'd and approved by @scoobinatural and @bibbidi-bobbity-booyah!! Thank you both <3

Dean Winchester sighed as he looked at himself in the mirror. He immediately wanted to smash the mirror upon seeing long, flowing blonde hair that was eerily similar to his mother’s. 

He’s been dead for… at least three months, down in Hell, and he comes back… only to be reentered in a Hell he left behind five years ago. 

He gently poked his chest. It hurt. He lifted his shirt up, thankful that no one was around, and nearly burst into tears. 

They were  _ back. _

He threw his shirt down, closing his eyes as the cruel and hateful comments he grew up with swarmed his mind once more. With trembling fingers, he popped open his jeans (which he’s noticed were too big for him) and looked down. All he saw was fine golden curls and no cock. 

He smashed the mirror with his fists, hating how slim and dainty his hands looked now. 

_ Does Henrietta think that she’s Henry? Silly girl, she could never be a boy.  _

** **

He hated the way Sam’s jaw dropped open when he saw him. But Sam- sweet, understanding, more of a girl than he’d ever be Sam- did nothing but wrap him up in his arms and whisper how much he’s missed his older brother. Dean clung to Sam, glad that he’s had his number one supporter since a twelve year old Dean told an eight year old Sam that he thinks he’s actually a boy. 

It was Sam who scrimped and saved to buy Dean a binder; it was Sam who consoled Dean before he managed to get on hormone therapy; it was Sam who bought Dean his first packer. The only time that Sam wasn’t there was when Dean had first his surgeries to make the full transition from Henrietta to Dean. Bobby, however, was there for that. 

He hated how Bobby’s eyes sharpened for an instance before the holy water was splashed on him, then softened when he realized that it really was Dean, just in a body he hasn’t seen in years. Still, he wrapped Dean up tight and whispered “Welcome home, son”. 

“I have no clue what happened, or how I got here,” Dean admitted, and the sound of the soft, sweet voice that he had gotten rid of grated on his ears. 

_ It’s just a phase; you’ll outgrow it, Henrietta.  _

** **

When Dean met the angel Castiel, the being who delivered him out of Hell, he had done several things. 

Stabbing him with the Kurdish knife Ruby had given Sam was one of them. 

Not believing that he was an honest to God Angel was another one. 

But shooting his gun at the angel the moment that Castiel let the name  _ Henrietta  _ cross his lips was the stupidest of all. 

“My name is Dean Michael Winchester,” he spat, Bobby looking at Dean as though he had lost his goddamn mind. “I am an Aquarius and I am a man.  _ You’re  _ the one who fucked up. If you’re the one who raised me out of Hell, then I wish you had left me back in there.” 

And with that, he turned on his heel and walked out, resisting the urge to swish his hips. 

_ Why can’t you accept the fact that you’re a very pretty girl, Henrietta? Do you know how many girls would kill for your looks?  _

** **

Sam didn’t say anything, just merely sighed as he walked over and began helping wrap the Ace bandages around Dean’s torso. 

“Where’s your binder?” his little brother asked softly. 

“I burned it. Burned all of it when I could after the surgeries,” Dean admitted. “Didn’t think I’d need them anymore.” He sniffled. “I hate this, Sammy. I hate this body. I hate everything about it.” 

“I know,” Sam said softly. “I’m sorry, Dean. I wish you didn’t have to go through this all over again. And soon, I’ll get you a new binder. I hate doing this, it’s so bad for you.”

Dean sniffled and leaned against his brother. “I wish I was back in Hell,” he whispered. 

Sam remained silent as he ran his fingers through Dean’s hair. “If it meant that you’re saved from this mental torture,” he said softly, “I wish you were back in Hell, too.” Then he brightened. “I know it’s not much,” he said shyly, “but… Can I cut your hair for you?” 

Dean looked up at Sam with a small smile. “Yeah. I’d like that,” he said quietly. 

_ You look like a boy. What if your boyfriend hates it?  _

** **

Castiel has since only deadnamed Dean three more times, profusely apologizing each and every time he sees that it visibly hurts Dean. Once, it was a very much accidental slip of the tongue, only to stop in the middle of the name and switch it to the simpler name. 

Dean liked the name. It was still a family name, since his maternal grandmother’s name was Deanna; it had a simple meaning of the word ‘valley’, and there was no way it could be mistaken as anything other than a boy’s name. 

Also,  _ Henrietta  _ was a fucking mouthful to say.

However, not everyone was as… accepting of the fact that Dean was very much a man trapped in this feminine body (that he can’t think of any perks for, except for maybe squeezing into smaller spaces and free drinks). 

Such as Zachariah. 

Stupid self ponticating asshole. 

“Henrietta,” Zachariah said in a patronizing tone. 

“Dean,” Castiel corrected softly. “His name is Dean.” 

Zachariah cut Castiel a look. “She was made as Father intended for her to be, which is a woman. There is nothing wrong with being a woman. Being a woman gives way to doing the most miraculous thing of all- give life. I’m sure that every woman wants a child- even the virgin Mary did, and she received her Son.” 

“How dare you presume to know Father’s intentions, when none of us-” Castiel was cut off by Dean’s warcry, a stolen angel blade in his hand as he charged Zachariah. Castiel immediately wrapped his arms around Dean and yanked him back (this was a  _ disadvantage  _ to being female, never mind the fact that Castiel is an honest to God  _ angel _ ). “DEAN NO!” 

“I AM INFERTILE, YOU MISERABLE EXCUSE FOR A SUIT!” Dean bellowed, his voice cracking. Tears streamed down his cheeks. “IF THAT’S NOT AN INDICATION THAT I’M SUPPOSED TO HAVE A FUCKIN’ DICK, I DON’T KNOW WHAT IS!!” 

_ Your poor future husband. No one will want you because you’re infertile.  _

** **

Dean knew that the world was fucked up when, after Sam, Bobby, and Castiel, the people most accepting of his transmasculinity were the  _ demons _ . 

Neither Alistair or any of the other various demons that they’ve encountered since Dean’s rise from the depths of Hell have deadnamed him. They may’ve stood there in shock at seeing Dean as a woman rather than a man, but then they’ve shrugged, recognizing his soul, and basically went “whatever” before continuing. A Winchester soul was a Winchester soul, no matter what gender it was. And Dean was still a fighter- albeit weaker due to the limitations of the female body, but a strong fighter nevertheless. 

Although Dean knew that if he was back in Hell, his torture would most likely be different. 

_ Miss Winchester, you are a young lady and you will act as such.  _

** **

Dean’s first period since he was sixteen came as a shock and a giant mess. No one carried pads, and the idea of shoving cotton up his vagina made Dean nauseated because  _ ew. _ That meant touching it. 

Also, the only reason they even  _ had  _ tampons was for nosebleeds and bullet wounds; not for actual menstruation. 

Dean hadn’t even  _ realized  _ that his period had came until hours after a hunt and he had peeled off his boxers to find his inner thighs soaked with blood. He had first thought that he had a stab wound, but closer inspection showed that it was actually his period and he ended up destroying the hotel room before collapsing into a ball and sobbing. 

Sam was the one who washed him clean and held him while Bobby went and got pads for him, because there was no way in Hell Dean was going to touch  _ that  _ more than he had to (and he only did when he was cleaning himself, because there was no way in Hell that he was going to get an infection there). 

“I hate this, Sammy, I hate it so much,” he sobbed messily into Sam’s flannel. “I want chocolate and Dr. Sexy.” 

“I know,” Sam sighed. “Come on, Bobby’s getting everything.” 

Dean wailed. “Can you massage me?” he whined. 

Sam nodded. “Of course, De.” 

The cramps lasted for days, and the flow was heavier than Dean’s ever remembered seeing it. Of course, he hasn’t seen it in years, not since he got on a strong enough dose of HRT and his hysterectomy done, but that was beside the point. His high dose of HRT and his parts being all back where they  _ didn’t  _ belong made this menstrual cycle particularly vicious, and stopped all hunts for the seals for a solid week and a half. 

_ You know that you may change your mind. It’s just a phase.  _

** **

Meeting Chuck Shurley may’ve been a lifesaver for Dean. If not also a headache. 

The author shared his love for alcohol, but he was such a bundle of anxiety that it could’ve hurt Dean’s brain. 

But recognizing the prophetic abilities where Chuck never deadnamed him or brought up that he was trans in his book series entitled “Supernatural”, other than a brief point where at one time, after he and Sam went back to Lawrence, Dean got a new birth certificate stating that a son, Dean Michael Winchester, was born to John and Mary Winchester on January 24, 1979. While he knew that having a trans character would’ve had a powerful statement, he didn’t think that the books would be as popular (or have even been printed) if that was a known fact. 

Plus, it was nice to know that, even in the sex scenes, the transmasc surgeries never seemed to bother the men he slept with. 

They brought Chuck along after they used him to scare Lilith off (due to the archangel protecting him) just in case she tried to seduce Sam (again, the demonfucker). Chuck wasn’t expecting it, but as long as he had his beloved typewriter, he didn’t seem to care. 

Chuck and Dean got close, and Dean reread the passage in the book where he got his new birth certificate again and again. 

Then, he realized something. 

_ Chuck must’ve never realized that he was trans. _

This swelled Dean’s heart and nearly made him cry. To know that from the onset, he was accepted as male and that it didn’t matter that he was trans, it wasn’t his entire character arc, made all the difference. Too many stories that Dean’s read about trans characters and other LGBT characters was that the sole purpose of them was to  _ be  _ LGBT. Entire storylines for those characters were  _ about  _ being trans or gay or a furry; to read a story where the character was basically implied to be trans, but it wasn’t the end all, be all of their being, swelled Dean’s heart. 

_ I bet that I could show you how good being a woman is. _

** **

“Chuck?” Dean asked one night. 

He and Chuck were sharing a hotel room while Sam had a room of his own for the night, to allow some privacy. They rotated, and it was Sam’s turn. 

“Hmm?” Chuck hummed in acknowledgement. 

Dean swallowed. “Can I tell you something?” 

“Sure,” Chuck said nonchalantly, turning in his chair from where he was typing rhythmically. 

It took Dean a few tries to say it, but Chuck waited patiently, not hurrying him. 

“I’m transgender. I was born a woman, but I am a man. Always have been,” Dean said in a rush. 

Chuck blinked, then shrugged. “Okay.” 

Dean cocked his head to the side in curiosity. The lack of “What the fuck” and questions concerned him. 

“I had a feeling when I reread you getting your birth certificate and had seen a couple of visions of you wrapping Ace bandages around your torso,” Chuck admitted, “but I chalked those up to other life events that I hadn’t seen. It makes no difference to me, Dean.” 

“It doesn’t?” Dean repeated.

“You’re Dean,” Chuck said. “And you’ve done some extraordinary things in your life. Whether you’re a man, a woman, or a genderless purple alien from Jupiter, it makes no difference to me. And it shouldn’t. Not to the people who matter most.” 

“Oh,” Dean said, flushing furiously. “It’s just… Okay, so, I had the surgeries done. Top and bottom. I did it when I started hunting without my dad and while Sammy was at Stanford. Scrimped and saved for both. Did a lot of research type things during recovery. And then I went to Hell. And when Cas raised me… Well, I guess he didn’t realize what he did and gave me back… well,  _ this _ ,” he gestured to himself disdainfully. 

“You’re a handsome individual, Dean,” Chuck said kindly. “No matter who you are.” 

Dean flushed some more and smiled at Chuck. “Thanks,” he said. “Uhh… you can get back to your writing, I guess. I just wanted to let you know.” 

Chuck nodded and sighed as he turned back to the typewriter. The comforting sounds echoed and Dean turned back to watching TV. 

_ No one will love you if you say you’re a man and not a woman, which is what you  _ are. 

** **

“Dean?” 

“Hmm?” Dean asked, looking up from  _ Mechanics Weekly.  _

“Are you… interested in sex at all?” Chuck asked hesitantly. 

“Why wouldn’t I be?” Dean asked in confusion. 

“Well, some people who go through medical transition find that they cannot decide on their sexual orientation,” Chuck explained. “That their sexual orientation shifts entirely, or goes completely nonexistent.” 

“I love sex,” Dean admitted with a flush. “Absolutely love it. When I was… when I was a teenager I thought I was bi.” 

“And now?” Chuck prompted. 

“Now, I’m gay as fuck,” Dean admitted. 

Chuck nodded. “Okay. I was just wondering.” 

Dean arched a brow. “People don’t ask that kind of question normally,” he said. 

“True, but I’m not most people,” Chuck replied casually. “You’re an attractive gentleman, and I’m bi. What’s the big deal?” 

Dean coughed and Chuck waited. “Sorry,” he said sheepishly. “Habit of writing- your sense of a filter goes away.” 

“It’s fine,” Dean croaked. “But do you…” 

“Do you?” Chuck asked plainly. 

Dean considered it for a few minutes, taking a look over the prophet. There was something… vaguely adorable about him, with his messy curls and his beard and his slight, seemingly unassuming appearance. Dean imagined fucking him (or being fucked by him) and couldn’t help the shiver that ran through his body. 

“Yeah,” he said. “I’d like that.” 

“Good.” Chuck stood up. “We’ll need supplies.” 

“Like what?” Dean asked as Chuck strode over to the hotel door. 

“Beer, Chinese food, a strap on, and plenty of lube,” Chuck said before leaving a furiously blushing Dean at the casualness in which Chuck delivered the information.

_ No one wants sex with a tranny.  _

** **

When Chuck returned two hours later, Dean was watching TV. He looked up at Chuck and flushed as he saw the large box in one hand. 

“I got your favorite beer,” Chuck admitted almost shyly. “And your favorite Chinese.” 

“Dude, did you get crab rangoons?” Dean asked excitedly. 

“I did,” Chuck said with a smile. “Smell ‘em? The Chinese restaurant up the street makes them fresh daily with no imitation crab meat.” 

The box and a smaller bag were set neatly aside as both Dean and Chuck decided that, at the moment, food and beer was  _ definitely  _ more important than sex. 

They ate and laughed and talked, curled up next to each other as though they had been dating. The whole encounter made Dean feel dizzy with happiness. Here was a reasonably attractive man who was an honest to fuck prophet of  _ God,  _ (although from the sounds of it the Angels had no clue where the fuck said God was), and who knew that Dean was trans and didn’t give a fuck. In fact, it just made them closer. 

Maybe Chuck, a self-proclaimed bi, preferred men over women in the bedroom and women in the romantic sense. Or maybe he was just completely attracted to Dean no matter what. 

He’s not sure, nor does he care to examine the reasons. All he knew was that Chucks fingers through his short hair made him feel good and that he was excited for the night that was yet to come. 

_ Why can’t you accept yourself the way that God made you? _

** **

Dean moaned as Chuck’s lips crashed against his, the stubble against Dean’s smooth cheek providing a delicious friction of pleasure. Dean wrapped his arms around Chuck’s shoulder, tugging him closer. Chuck’s lips were tinged with the taste of good Chinese and warm beer, and Dean chased after it hungrily, pressing himself into the older man. 

“Patience, Dean,” Chuck murmured lowly. “We have all night.” 

“It’s been far too damn long for me, Chuck,” Dean moaned, “I need it, Chuck, please.” 

Chuck easily manhandled Dean down onto the bed and pressed him into the mattress, looking down at Dean hungrily. And Dean, knowing Chuck for who he is as a person, knew that the hungry look was for Dean, was for Dean’s true person, and not the flesh prison that he had been so cruelly trapped in. Blue eyes burned fervently as he raked his eyes over Dean. 

“Gorgeous,” he whispered. “Absolutely gorgeous. And all mine to have. Isn’t that right, Dean?” 

Dean’s mouth went dry and he nodded. “Yeah,” he whispered softly. “Yeah, all yours.” 

Chuck leaned in and gave Dean a soft, sweet kiss. “Want to get ready?” 

“God, yes,” Dean breathed. 

Chuck smirked and kissed Dean again. “Just ‘Chuck’ will do,” he teased playfully.

Dean laughed and sat up as Chuck got up from the bed and went over to grab the box and the small bag from the local adult store. He set the box down in front of Dean. Dean reached over and grabbed his knife from under his pillow. At Chuck’s raised eyebrow, he shrugged. “I fight the things that go bump in the night. Having a knife on hand is handy, especially when the blade’s silver and the hilt’s made out of iron.” 

“Fair enough,” Chuck said. 

Dean used the knife to open the box and pulled out the obnoxiously colored highlighter yellow strap on with a black harness. He raised his brow at Chuck. 

“It’s all that they had, and we’re a bit pressed for time,” Chuck admitted. “Apologies.” 

Dean stared at Chuck, trying to not be happy- after all, who wants to fuck somebody with a toy that looks like it could direct traffic? He couldn’t. He burst into giggles. 

Chuck laughed with him, the two of them laughing at the situation. A hunter and a prophet, getting together for sex, and they’re using a highlighter yellow strap on in a dirty hotel room that had definitely seen better, cleaner days.

It didn’t dampen the arousal at all, however. In fact, it seemed to heighten it as both Dean and Chuck fell into unclothing each other. Chuck didn’t even seem to notice the binder that Sam had managed to buy off the internet with some sort of wizard powers (Dean’s fairly certain that the remote cabin that they were staying at didn’t even have a LAN connection, much less WiFi) and had ran his hands over Dean’s mostly naked torso reverently, even as Dean jimmied the button of Chuck’s jeans and shoved them down his thighs, revealing dark grey boxers. 

“So eager, young one,” Chuck laughed as he leaned in to nip at Dean’s neck, pressing him back down into the bed. “Let’s get you undressed, sweetheart, and get you situated.”

Dean melted and pawed playfully at Chuck. “I wanna see you,” he said. “Please.” 

“You will,” Chuck shushed the younger man as he undid the button of Dean’s jeans. “You will, sweetheart. Just lay still for me.” 

He slowly undid the zipper and pulled down the jeans. Dean’s breath caught in his throat and he held it, hoping that Chuck wouldn’t be… well, revolted or whatever. 

He wasn’t. All Chuck did was press a tender kiss on Dean’s thigh and smiled before looking up at him. “Want to hand me the toy?” he asked, holding his hand out for it. 

Dean grabbed it and nearly hit Chuck in the face with it, both of them giggling at the color. 

It was  _ fun.  _ It was  _ playful. _ It was everything that Dean could hope for as a sexual experience. Fun, sexy, playful. Being able to laugh but melt; being able to smile but gasp. 

Chuck tapped the side of Dean’s thigh to raise his legs, letting the harness slide up the smooth legs (and Dean, male or female or whatever,  _ loved  _ having smooth legs) and settle over Dean’s hips. The color of the dildo was definitely obnoxious, but Dean almost didn’t care as he stretched and he hissed. He had been wearing his binder all day; he shouldn’t have, but he just felt better with it on than he did with it off. 

“Are you okay, sweetheart?” Chuck asked softly, brushing his thumb over Dean’s cheek. 

“Binder’s digging in a little bit,” Dean admitted softly. “I just… I don’t want to take it off.” 

“How long have you had it on?” Chuck asked seriously. 

Dean considered it. He woke up at four this morning, they ran some errands, they did some research, they blocked a demon from unlocking another seal, they had lunch, they got rid of a restless spirit… “About sixteen hours,” he admitted softly. 

“Dean,” Chuck gently admonished. 

“I know,” he sighed. “I know I shouldn’t have, but-” 

“But it’s not healthy,” Chuck whispered. “Did you sleep in it?” 

Dean shook his head. “Nah,” he whispered. “Put it on as soon as I got up.” 

Chuck leaned in and kissed Dean. “Please, take it off,” he said. “I don’t want you to be hurt.”

“You won’t-” Dean was silenced by Chuck’s gentle finger on his lips. 

“If you don’t want me to touch them, I won’t,” Chuck promised. “If you want to grab something so that there’s cloth separating them, I wouldn’t object. I want you to be comfortable while also not compromising your health.” 

Dean bit his lip and looked up at Chuck trustingly. “I’m scared,” he whispered. He hasn’t had boobs in so long, he’s forgotten what it’s like to even have them in an intimate setting; between HRT and his top surgery, he didn’t need to worry about them. Now, he did, and he was worried and scared. 

“It’s okay to be scared,” Chuck soothed. “But I’m here. I’ve known, and I’m not running, am I?” 

Dean shook his head. 

“See? I don’t care. I want to make you feel good, Dean,” Chuck whispered. “I want your body to light up as I help you reach completion. I want you to moan and buck and be who you are. What body you’re in doesn’t matter to me. I just want you to take care of yourself.” 

Dean’s entire body warmed at Chuck’s words and he gave a small smile. “You won’t touch?” he whispered. 

“I won’t touch,” Chuck promised. “Not unless you give me permission to. Do you need help?” 

Dean hesitated, then nodded, blushing furiously. 

Chuck kissed a reddish-pink cheek and reached to undo the binder gently, setting it to the side neatly as he ran his hands down his side. Dean didn’t look down to watch. He didn’t want to see his breasts. 

The only thing he liked about them (besides using them to get free drinks and hustle pool) was the nipples, because they were sensitive. However, after his top surgery, they deadened. Now the sensitivity was back, but he didn’t care. He just wanted them gone. 

He’s also thankful that they were relatively small. Mostly because on the days he decided to bind for a very long period of time, he could get away with no bra or binder on the next day. It just  _ hurt  _ to do so. 

He took a few deep breaths as he felt his ribcage expand, large gasping breaths and Chuck waited patiently, watching as Dean got comfortable in his skin again. 

“They’re beautiful,” Chuck whispered, “but I can see how much pain they cause you.” He reached up and gently caressed Dean’s cheek and Dean leaned into the touch. “I wish that there was something I could do about it.” 

Dean smiled and leaned into Chuck, kissing him. The toy bounced between them, but neither of them cared as Chuck gently pressed Dean back down into the mattress, sliding his leg over and straddling the younger man. 

“How quiet do we have to be?” Chuck whispered. 

“Oh, Princess can deal with the noise,” Dean scoffed. “It’s been far too long for either of us. Make me scream, Chuck.” 

“With pleasure,” Chuck purred as he slicked up his fingers and reached behind him. Dean could only watch as Chuck’s mouth dropped open in pleasure as he slid two fingers deep into him. 

“Fuck,” he whispered. “I haven’t done this in too long.” 

“It’s been far too long for the both of us,” Dean agreed, watching as Chuck fingered himself open. He watched Chuck’s face relax in pleasure; he watched the way the aroused flush extended past his face and neck and onto his chest; he watched the large cock in front of him bounce, a pearl of pre-cum on the head. Feeling a bit impish, Dean leaned forward and licked the bead away, making Chuck gasp. 

“Brat,” he teased playfully, groaning loudly suddenly. 

“Did you hit your prostate?” Dean asked breathlessly. 

“Yeah,” Chuck admitted with a hoarse laugh. “Fuck, I need you in me.” 

“Then,” Dean reached for the lube himself and slicked up the false phallus. “Save a horse, ride a Winchester.” 

“Dean,” Chuck laughed, “even you have to admit that that was  _ abysmal _ .” 

Dean grinned and nodded. “I do admit it,” he said. “But it’s true. I want you to ride me, Chuck. Please.” 

“Then I’ll ride you,” Chuck breathed. He shimmied backwards and grabbed the dildo firmly in his hand. Dean could only watch breathlessly as Chuck slowly descended, his hole swallowing the bright yellow dick.

“Fuck, we got a thick one here,” Chuck groaned as he squirmed. Dean reached up and rested his hands on Chuck’s hips, guiding him down. 

“God, you look so good,” Dean breathed as he watched Chuck settle down all the way. “Holy fuck.” 

“You like this?” Chuck smirked. “Wait until I actually begin riding you, sweetheart.” 

Dean groaned and ran his fingers over the soft, tender skin of Chuck’s hips, admiring the way his body looked hovering above him, impaled on the admittedly cartoonish cock. Chuck looked like a God, a God of Sex, and Dean was his willing sacrifice. 

“Move,” he commanded. “Please.” 

“As you wish,” Chuck whispered, beginning to ride up and down the strap on. 

Dean could only watch, mesmerized, watching Chuck use him for his pleasure, with his permission. His hands roamed up and down his thighs, his ass, his hips, his stomach, never touching the other man’s cock, just admiring the sensual beauty of the older man. 

And  _ God,  _ did Chuck look hot like this. His curls were becoming unraveled and were sticking to his forehead by the soft sheen of sweat upon his brow; his skin was flushed with arousal and painted over his face, neck, and chest; his muscles flexed as he rode Dean… it was arousing and intoxicating to watch. Dean could feel his female body responding urgently, but he didn’t care about that. It meant he was feeling  _ good,  _ watching Chuck get himself off. 

“You’re beautiful like this,” Dean whispered. “God, so fuckin’ hot.” 

“You are, too,” Chuck breathed, looking down. 

Dean sat up and brought Chuck in for a slow, deep kiss full of passion and need. The need to make Chuck feel amazing, to make him orgasm like he never had before. Dean got off on getting other people off, and it saved him numerous times back when he wasn’t out and having sex prior to his surgeries. 

Chuck responded, cupping the back of Dean’s head and deepening the kiss, nipping at Dean’s tongue as Dean ran his hands up and along Chuck’s biceps, pulling him closer to him. 

Chuck still rode Dean as they made out, caressing each other like they had all the time in the world. They could distantly hear the TV from Sam’s room next door, hear the wind howling outside. It was a cooler night, but Dean knew tonight he wouldn’t need any blankets, not with the hot sex that was happening and knowing he had a warm body to sleep next to that night. He would be plenty warm, both inside and out. 

Without warning, he flipped them, so that Chuck was on his back. The older man gasped and looked up at Dean with wide eyes as Dean began powerfully thrusting into him, aiding him was youth and vitality. 

“Needed a new position,” Dean said innocently as he thrusted powerfully into Chuck. The harness didn’t dig in at all, and if it wasn’t for the obnoxious color, Dean felt like he had his own cock that he was driving into Chuck. 

Chuck huffed, then moaned as Dean shifted his hips. He gasped on the next thrust. 

“Did I find your sweet spot?” Dean asked gruffly as he continued to pound Chuck, chasing his release, making Chuck chase his. 

“Yes, fuck, yes, Dean!” Chuck cried out. His nails raked down Dean’s back and Dean hissed, arching into the grip. 

“Then enjoy, ‘cause I sure am,” Dean grunted. 

Chuck continued to writhe underneath Dean. The leaking of his cock against Dean’s stomach told him that he was close, so very close. Just a few thrusts away from covering them in wet, sticky release. 

“Cum for me, Chuck,” Dean whispered. “I need you to cum for me. I’ll take my pleasure in yours.” 

“Dean-” Chuck gasped loudly, his back arching. 

“Come on, cum for me,” Dean coaxed. “I promise. I’ll get my pleasure from you getting yours.” 

Chuck came, and Dean groaned, feeling his own body responding. Chuck’s release was white hot against his stomach and he gave a cry. Dean thought that he was the most beautiful thing he had ever seen, after Sam being born.

He ignored the way that he came, wishing he had a dick still (especially for the  _ clench  _ factor), but watching Chuck from being pegged? 

Priceless. 

The two fell into a boneless heap, kissing and calming down from their respective highs. Dean cupped Chuck’s face and smiled at him. 

“Thank you,” he murmured. 

“No, Dean, thank  _ you, _ ” Chuck smiled. “Really. It was hot.” 

Dean flushed and nuzzled against Chuck’s beard. 

“Now, pull out, big boy,” Chuck said, patting Dean’s ass. “Let’s get cleaned up and get some sleep.” 

“Not up for another round?” Dean teased. 

Chuck laughed. “Not yet,” he said. “Perhaps in the morning.” 

Dean laughed and pulled out, groaning as he slipped the harness off and threw the offensively colored dildo across the hotel room. 

Chuck snorted and got up to grab a washcloth to clean the two of them up. 

The rest of the night was passed with quiet words and tender kisses, neither man really wanting to sleep but both of them realizing that they needed it. When they finally did drift off, Dean was curled up neatly in Chuck’s arms, and he proceeded to have the best night’s worth of sleep in a long time. 

** **

Dean woke up groggily and he snuggled more into Chuck. 

“Good morning, Dean,” Chuck smiled, running his fingers through his hair. 

“Morning,” Dean said roughly, then paused. That… that sounded like his voice after the surgeries and two years. 

He threw back the covers, ignoring Chuck’s protests, and gaped. 

He had a man’s body. Not a body that was at one point a woman’s and had been turned into a man’s, but an actual, honest to God, man’s body. Dick and balls and hairy legs and all. 

He ran his hands up and down his body, not seeing the warm, soft smile on Chuck’s face as he watched. He gave a whoop and got up to look at himself in the mirror in the bathroom. He even had stubble on his face again. 

“God, you’re awesome,” he breathed, not daring to believe it or realizing he was thanking the man that had laid next to him. 

“You’re beautiful, Dean,” Chuck hummed. He had gotten up and smiled at Dean. “This form suits you very well.” 

Dean turned and looked at Chuck with a smile. “You feel up for another round, champ?” he asked happily. 

“Only if you’re the one doing the fucking,” Chuck smirked. 

“Oh  _ hell  _ yeah.” Dean followed Chuck back to bed. 

_ I am Dean Michael Winchester, and I am wholly me.  _

**Author's Note:**

> Tumblr: @lucibae-is-dancing-in-hell
> 
> Twitter: @Alendra_Dragon
> 
> Comments and Kudos are Shiny!!


End file.
